


Oh, Sammy

by reluctantabandon



Category: Supernatural
Genre: Anal Play, Anal Sex, Established Relationship, Kinda, M/M, Sam wearing these, Underage - Freeform, Wincest - Freeform, cross-dressing, only slightly though, sam in women's underwear
Language: English
Status: Completed
Published: 2014-02-07
Updated: 2014-02-07
Packaged: 2018-01-11 12:21:31
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,874
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1173011
Author URL: https://archiveofourown.org/users/reluctantabandon/pseuds/reluctantabandon
Summary: <blockquote class="userstuff">
              <p>Sam finds something left behind in their motel room.</p><p>(Sam is 17, Dean is 21. Just, you know, pretend John is off on a hunt or something.)</p>
            </blockquote>





	Oh, Sammy

**Author's Note:**

  * For [Bskizzle](https://archiveofourown.org/users/Bskizzle/gifts).



> Okay, so I wrote this and posted it on tumblr at 1:30 am in a drunken stupor! This one goes out to bskizzle, because she was having a shit day; to Winter, she knows why; and to samschickhair.tumblr.com, who made a delightful post under her sam wearing these tag and inspired me to smut!

They were in the room when they checked in. The bag had been pushed under the bed; Sam only found it because his pocketknife had bounced out of his pocket and away from his clutching hand.

It was a plain brown bag. Very discreet. He pulled it out, thinking it was empty, thinking he’d throw it away. It wasn’t, though; not by a long shot.

When he reached in and pulled them out, his breath caught. Sam could feel his cheeks burn, hot then cold, and he swallowed and stuffed the bag in his duffel. For later.

He just wanted to see. Just wanted to try. It wasn’t really a new thing, not really; he and Dean had played, once or twice, just for fun.

He spent the next couple of hours studiously ignoring his duffel bag.

Then Dean went out for pizza.

As soon as the door shut behind Dean, Sam got up and reached for his bag. The brown paper crackled in his hands, echoing the electric charge zinging up and down his spine. God, what would Dean say? He couldn’t wait to find out — his breathing shortened, and he felt a little off-balance, a little drunk.

He pulled the stockings out first. Blush pink, so sheer he could see the lines on his palm when he opened the packet. And yeah, extra-tall — it’s like someone had been waiting for him to find them. Soft, delicate satin ribbon bows adorned the top of each, wide ribbon gleaming in the lamplight. He smoothed them out, set them on the bed next to him. Swallowed again.

The panties came out next. God, they were perfect — Sam couldn’t get his jeans down fast enough, toed off his boots and whipped his socks and boxers off. The same blush pink as the stockings, softest satin with a sweet little lace panel on the front, embroidered with tiny rosebuds, each with a miniscule green leaf. Sam pulled them up over his legs, thanking the powers-that-be that Dean had shaved him just that morning. They slid smoothly up over his tight ass, snug and just the right amount of confining over his swiftly hardening cock. God, they were lovely, and the wet head of his dick just peeked out over the tiny bow at the very front.

The stockings had a nice wide elastic top, not too tight, and Sam very carefully pulled the sheer fabric up over his calves, loving the way the material hugged his skin, how the perky bows sat so delightfully right under the curve of his ass. He wished for a fleeting moment that he had some darling shoes to wear, too, but those would have to wait for later. In the meantime, what else?

Sam shrugged out of his blue flannel shirt and lifted the grey t-shirt over his head. He could feel his cheeks still burning, his breath short and swift in anticipation. He took a few steps toward Dean’s bag, reveling in the feel of the satin against his hot skin, the mesh of the clingy stockings on his calves and ankles. He rummaged through Dean’s duffel, finally pulling out a white t-shirt that was soft and worn thin with washing. Sam pulled the shirt on over his head and took a deep breath.

Stepping into the bathroom, he flicked on the light. His own wide-eyed face looked back at him from the mirror, cheeks pink, mouth slightly open. The shirt strained across his shoulders, showed his nipples, flushed nubs dark and hard against the fabric. The hem barely reached his waist, and he turned, looking over his shoulder to see the full effect of panties and bows. He had to palm himself thinking of Dean’s face when he saw. God. Dean was taking forever; how long did it take to get a fucking pizza, anyway? Sam smoothed his hands downward from waist to thigh, watching himself in the mirror, imagining how Dean’s hands would feel against soft cotton, silk satin, how he’d touch the —

The outer door opened, then shut with a rattle. Sam gave Dean a moment to put down the pizza.

“Sammy?”

“Dean.” Sam stepped through the bathroom door.

“Fuck.” Dean swore, dropping his jacket to the floor. “Jesus, Sam.”

Sam loved the way Dean looked at him like this: like he was something precious, breakable, edible. Dean stalked a few steps closer, eyes raking Sam’s body, lingering on the tops of the stockings and on Sam’s cock, harder now and dripping, messing up the lacy front of the panties. Sam looked at Dean from beneath his lashes, feeling the hot-cold shakiness of anticipation, nerves, a tiny, delicious bit of shame. He shivered.

Dean stepped up, closing the distance between them, placing his hands gently on Sam’s upper arms, soothing. Sam breathed out, and Dean caught his mouth in a sweet kiss, reverent and undemanding. Sam could feel Dean’s heart, pounding so close to his; could feel the heat of him, tight and hard in his jeans. He wondered if slow and sweet would last. He leaned into the kiss, wanting more, flicking his tongue against Dean’s lush bottom lip.

Dean made a hurt noise and opened for him, wanting as much as Sam, one hand moving to cup the back of Sam’s head, pull him closer, the other sliding down to drag fingertips along the waistband of the tiny panties.

“God, Sam, m’not gonna —” Dean gasped against his mouth “—not gonna last long. So hot. Jesus, your mouth. God, just let me —” and Dean sank slowly to his knees, mouthing at Sam’s chest, his belly, dipping his tongue into his navel, shaking fingers skimming along the satin fabric. He nuzzled into the crease of Sam’s groin, breathing hot through the lace, hands sliding around to finally, finally cup Sam’s ass, and Sam had to put his hands on Dean’s shoulders to steady himself as Dean wormed his tongue under the waistband and sucked the head of Sam’s cock into his mouth.

“God, Dean, oh,” Sam moaned, eyes shut, head falling back. Dean pulled the elastic down and snugged it right up under Sam’s balls, and Sam’s hands tightened as Dean’s lips slid down further over his length. One of Dean’s hands came around to fondle the soft skin of his sac, and the other danced fingers down the curve of his thigh, encountered the ribbon and...stopped.

Dean pulled off Sam’s cock with a loud smack, eyes wide as he looked up at Sam’s flushed face.

“Oh, you have _got_ to be kidding me,” he breathed, running both hands now up the backs of Sam’s taut calves to the tops of the stockings. “Oh, Sammy. Baby boy.” And with a rush and a heave, Dean stood, lifted Sam by the thighs, and threw him onto the bed.

Sam bounced once, stunned, reddened mouth a perfect O of surprise. Dean, never taking his eyes off him, shed boots, flannel, t-shirt and jeans and then was on him in a microsecond. He bore Sam down into the bed, licking and sucking at the column of his neck while Sam panted beneath him, hands everywhere, arching up and winding his legs around Dean’s. Dean groaned again and bit, hard.

Sam cried out and arched further, and Dean gave him one last nip and knelt back. Sam whined at the loss of contact, but then Dean gathered him up, all flushed and pink and pretty, and flipped him neatly onto his stomach.

“Sammy,” Dean breathed, and Sam felt the gentle brush of Dean’s hands on the backs of his legs, tiny tug of ribbon slipping through his fingers. Then, those hands were under his hips, jerking him up and back, so he was on his knees with his ass in the air, panting with need. Dean disappeared for a second, and Sam could hear him rummaging through his bag, heard the thump of the lube bottle as he threw it on the bed. Then Dean was on him again.

“God, _Dean!_ ” Sam moaned and writhed as Dean’s thumbs dug into his ass cheeks, pulling him apart, and he felt Dean’s tongue, slick and wet through the cool silk. It was maddening — too much, not enough, and Sam squirmed backward, wanting more, pressure and heat and liquid slide. Dean teased, circling his hole with the tip of his tongue, then when Sam felt like he absolutely couldn’t take any more, Dean’s fingers slid through the leg-hole of the panties and pressed in.

Sam shoved backwards, and Dean chuckled. “Greedy little thing. Hold on, baby boy, I’ve got you.” Sam felt the first delicious burn and slide as Dean’s lubed finger entered him, and heard Dean’s stifled groan. Felt an open-mouthed kiss to his thigh. “God, you’re so ready. God, Sam, need to fuck you.”

“Yeah, Dean, _please!_ ” Sam sobbed, grinding back onto Dean’s hand. Dean had two fingers in, now, twisting, and Sam panted, cock hard and leaking on the bedspread. “Need you, need you inside me.”

“Gonna fuck you good, sweetheart, gonna leave these on you, wanna feel them on you when you come on my cock,” Dean panted, and Sam felt him pull the fabric forward, back up and over Sam’s cock, then felt the pressure as Dean pulled the crotch to one side, baring his hole. Then the hot, blunt head, and Sam was opening up, moaning, clutching the bedspread as Dean pushed his way inside. Dean’s cock felt huge, splitting him open even as he rocked back to take more, faster.

Dean bottomed out and just held Sam there, panting, Sam doing his best to grind back, arching and wriggling. Dean ran his hands one last time down the backs of Sam’s thighs, stroking and flipping the bows, then dug his fingers into Sam’s hips and started slamming into him. Sam cried out with each thrust, keening into the pillows, feeling the pull and drag of the fabric, the elastic, the soft scratch of the lace, and then Dean found his sweet spot and hit it over and over and Sam felt the prickle and rush wash over him and he was coming, coming, twisting and sobbing into the covers.

Then Dean’s arm was around his chest, and Dean hoisted him up. He knelt back until Sam was sitting on his cock, legs splayed out to either side of Dean’s, his head back on Dean’s shoulder. Dean’s arm was hard around him, holding Sam up as he rammed into him from below, murmuring into his ear, telling him how hot, how good he was, how Dean would take care of him, always. Then Dean stiffened and groaned, and Sam felt the pulse of his cock inside him, liquid and hot, and he cried out again at the perfection of it all. Together they fell forward, breathless, collapsing in a heap on the rumpled covers.

In a few moments, Dean was stretched out alongside him, pulling Sam into the curve of his front. His fingers played idly with the satin bows, dragging their ends through his fingers.

“Baby boy,” Dean murmured, kissing the back of his neck. Sam sighed and snuggled closer. Sleep, now, for sure, but he had the feeling they’d be doing that again real soon.

**Author's Note:**

> Completely and totally unbeta'd and on two shots of bourbon. So sue me.


End file.
